Diisopropylethylamine → 2-{[4-(1,3-Thiazol-2-yl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine

HRID 1828300Notes

Reaction equation

HRID 1828300 reaction equation
Cl[CH2:2][C:3]1[S:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][N:6]=2.[S:12]1[CH:16]=[CH:15][N:14]=[C:13]1[N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.CCN(C(C)C)C(C)C>>[S:12]1[CH:16]=[CH:15][N:14]=[C:13]1[N:17]1[CH2:18][CH2:19][N:20]([CH2:2][C:3]2[S:4][C:5]3[C:10]([N:11]=2)=[CH:9][CH:8]=[CH:7][N:6]=3)[CH2:21][CH2:22]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 9118061-(Thiazol-2-yl)piperazineHCID 142042072-(Chloromethyl)-[1,3]thiazolo[5,4-b]pyridine

Product 1

HCID 117233632-{[4-(1,3-Thiazol-2-yl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine

Procedure

The product from Example 38A (200 mg, 1.1 mmol), 1-(1,3-thiazol-2-yl)piperazine (219 mg, 1.3 mmol), and DIEA (340 μL, 2.1 mmol) were processed as described in Example 38B to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.71 (m, 4H) 3.46 (m, 4H) 4.06 (s, 2H) 6.86 (d, J=3.73 Hz, 1H) 7.17 (d, J=3.73 Hz, 1H) 7.56 (dd, J=8.14, 4.75 Hz, 1H) 8.33 (dd, J=8.14, 1.70 Hz, 1H) 8.59 (dd, J=4.58, 1.53 Hz, 1H). (ESI) m/z 318 (M+H)+.

Sources & evidence

ORD record
ord-75bbce69b3c24bae971a00e13c474df2
Source dataset
uspto-grants-2006_06
Patent number
US07057042B2

Reaction notes

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